Select the month that you will be traveling from the table below to view the packing list:
What Ashland is like to visit throughout the year:
January
When visiting Ashland in January, be sure to pack layers and warm clothing. The temperatures can drop to below freezing at night, so a warm winter coat, hat, and gloves are essential. During the day, the weather can be quite mild, so having layers that you can easily take off and put on is key. Don’t forget to bring a sturdy pair of walking shoes for exploring the town and its surrounding trails. In terms of attire for visiting the famous Oregon Shakespeare Festival, it’s best to dress comfortably but also look presentable. Many locals and visitors opt for business casual attire, but you’ll also see a mix of casual and formal clothing as well. The theaters can get quite warm, so bringing a light sweater or shawl is a good idea. And don’t forget your rain gear! Ashland is known for its rainy winters, so be prepared with a waterproof jacket and umbrella. With these tips in mind, you’ll be able to fully enjoy the beauty and culture of Ashland in January.
January in Ashland is a time of tranquility and reflection, making it the perfect escape for travelers seeking a peaceful getaway. One must-see activity during this time is attending a performance at the renowned Oregon Shakespeare Festival. With fewer crowds and discounted tickets, it’s the ideal opportunity to immerse yourself in the world of Shakespearean theater. After the show, take a stroll through the charming downtown area, lined with eclectic shops and cozy cafes, and grab a warm cup of coffee to savor the winter ambiance. For outdoor enthusiasts, January in Ashland offers a plethora of activities to enjoy. Bundle up and take a hike through the picturesque Lithia Park, or hit the slopes at the nearby Mt. Ashland ski resort. After a day of outdoor adventure, warm up with a visit to one of the local hot springs, such as Jackson Wellsprings or Lithia Hot Springs. And for a unique cultural experience, don’t miss the annual Chinese New Year celebration in Ashland, complete with traditional dragon dances, lantern festivals, and delicious food. January may be the quiet season in Ashland, but it’s full of charm and hidden gems waiting to be discovered.
February
As you plan your trip to Ashland in February, it’s important to consider the unpredictable weather of southern Oregon. The Pacific Northwest is known for its rainy winters, so be sure to pack a waterproof jacket and sturdy shoes for exploring the charming streets of downtown Ashland. Layering is key, as the temperatures can vary greatly throughout the day. Bring a warm sweater or fleece to wear under your jacket, and don’t forget a scarf and hat to keep you cozy. And while it may not be the most fashionable choice, a pair of rain boots will come in handy for any outdoor activities or hikes you have planned. When it comes to dressing for the theater, Ashland’s renowned Oregon Shakespeare Festival is a must-see attraction. For evening performances, a nice pair of jeans or slacks paired with a dress shirt or blouse will fit in perfectly with the casual yet sophisticated atmosphere. And don’t forget to bring a dressy outfit for the fancier restaurants in town. As for what to bring, don’t forget your camera to capture the stunning natural beauty of the Rogue Valley, as well as your appetite for the delicious local cuisine. And of course, be sure to bring an open mind and a sense of adventure to fully embrace all that Ashland has to offer.
February is the perfect time to visit charming Ashland, Oregon. This small town is nestled in the scenic Rogue Valley and boasts a thriving arts and culture scene. One of the highlights of this time of year is the annual Oregon Chocolate Festival, where visitors can indulge in all things chocolate, from truffles to hot cocoa. The festival also features cooking demonstrations, workshops, and even a chocolate spa. It’s a must-visit for any chocolate lover. Aside from the chocolate festivities, February is also the prime time to catch a performance at the renowned Oregon Shakespeare Festival. This world-class theater company puts on a variety of shows throughout the month, including classic Shakespeare plays as well as contemporary works. The intimate theater setting allows for an immersive experience and the talented actors never fail to impress. And after a night at the theater, be sure to stroll through Ashland’s charming downtown, complete with quaint shops, delicious restaurants, and cozy cafes. February truly is a magical time to experience all that Ashland has to offer.
March
When visiting the charming town of Ashland in March, it’s important to dress in layers and be prepared for varying weather conditions. The mornings can be chilly, with temperatures in the low 40s, but by midday, it can warm up to the mid to high 60s. I recommend wearing comfortable walking shoes, as Ashland is a pedestrian-friendly town with many shops, restaurants, and parks to explore. A light jacket or sweater is also a must, as evenings can cool down quickly. In terms of what to wear, a casual and relaxed style is appropriate for exploring Ashland. Locals tend to dress in a laid-back and practical manner, so leave your fancy clothes at home. A pair of jeans or khakis paired with a comfortable t-shirt or blouse is a great choice for both men and women. Don’t forget to bring a rain jacket or umbrella, as March can bring some rain showers to the area. And of course, don’t forget to bring a camera to capture the beautiful scenery and vibrant culture of Ashland.
Ashland, Oregon is a charming town nestled in the beautiful Rogue Valley. While known for its famous Shakespeare Festival, there are plenty of other activities to enjoy during the month of March. Start your day by exploring the Lithia Park, a picturesque green space with walking trails and a duck pond. In the evening, catch a performance at the Oregon Cabaret Theatre, known for its lively musical productions and delicious food. For a taste of Ashland’s local culture, be sure to visit the Ashland Art Center. This vibrant community space features the work of over 200 local artists and hosts events such as art classes and live music. For a unique experience, take a short drive to nearby Jacksonville and hop on the historic trolley for a tour of this quaint town. And of course, no visit to Ashland is complete without indulging in some of the town’s famous chocolate at the artisanal shop, Lillie Belle Farms. With its small town charm and lively arts scene, Ashland is the perfect destination for a March getaway.
April
As April is the shoulder season in Ashland, packing for your trip can be a bit tricky. The weather can be unpredictable, so it’s important to bring layers and be prepared for both warm and cool temperatures. I recommend bringing a light jacket or sweater, as well as a rain jacket or umbrella, just in case. Comfortable walking shoes are a must, as Ashland is best explored on foot. Don’t forget to also bring a hat and sunglasses for those sunny days. When it comes to dressing for activities in Ashland, the key is to be practical yet stylish. As the city is known for its vibrant arts scene, you can’t go wrong with a pair of comfortable jeans paired with a nice blouse or button-down shirt. For a more formal evening at the Oregon Shakespeare Festival, a dress or collared shirt and slacks are appropriate. And of course, don’t forget to pack a swimsuit for a dip in the nearby lakes or hot springs. Overall, dressing in layers, being prepared for the weather, and incorporating a touch of artistic flair into your outfits will ensure you fit right in with the eclectic and creative vibe of Ashland.
April is a magical time to visit the charming town of Ashland, Oregon. As the days get longer and the flowers begin to bloom, the town comes alive with a vibrant energy. One of the highlights of April in Ashland is the famous Shakespeare Festival, which kicks off its season with a variety of performances ranging from traditional Shakespeare plays to contemporary productions. With multiple theaters and an outdoor stage, this festival is a must-see for any lover of the arts. Aside from the Shakespeare Festival, April is the perfect time to explore the natural beauty of Ashland. Take a hike through Lithia Park, a 93-acre oasis in the heart of the town, and be surrounded by colorful wildflowers and towering trees. For a more leisurely experience, stroll through the quaint downtown area and browse the local shops and cafes. And don’t forget to indulge in some delicious farm-to-table cuisine, as April marks the start of the growing season for the local farms. No matter what your interests may be, there is something for everyone to enjoy in Ashland during the lovely month of April.
May
When visiting the charming town of Ashland in May, it’s important to dress for both comfort and style. The weather can vary greatly during this time, so it’s best to bring layers. A light jacket or sweater is perfect for cooler mornings and evenings, while a t-shirt and shorts will keep you cool during the warmer afternoons. Don’t forget to pack a rain jacket or umbrella, as May can bring occasional showers. Comfortable walking shoes are a must, as Ashland is a pedestrian-friendly town with many cobblestone streets and hilly terrain. In addition to dressing appropriately for the weather, it’s also important to dress respectfully when visiting Ashland. This quaint town is known for its arts and culture, and many visitors come to see the famous Shakespeare Festival. When attending a play or visiting one of the many galleries or museums, aim for a stylish yet casual look. Opt for dress pants or a flowy dress paired with comfortable shoes. And don’t forget to bring a small backpack or crossbody bag to carry your essentials, as Ashland’s streets are best explored on foot. With the right clothing and accessories, you’ll be ready to fully immerse yourself in all that Ashland has to offer.
May is a delightful time to visit Ashland, a charming town nestled in the picturesque Rogue Valley of Southern Oregon. As the weather warms up, the town comes alive with spring blooms and outdoor activities. One of the top things to do in May is to attend the world-renowned Oregon Shakespeare Festival. Every year, the festival presents a diverse selection of plays and performances, ranging from classic Shakespearean dramas to contemporary works. With multiple theaters and beautiful outdoor venues, it’s a treat for theater lovers and a must-do for any visitor to Ashland. Aside from the festival, May is also a great time to explore Ashland’s natural beauty. Take a hike through the stunning Lithia Park, located in the heart of the town. The park boasts lush forests, bubbling streams, and peaceful ponds, making it a perfect escape from the hustle and bustle of everyday life. For a more adrenaline-filled adventure, head to nearby Mt. Ashland for some hiking or mountain biking. With stunning views and challenging trails, it’s a popular spot for outdoor enthusiasts. And after a day of exploring, don’t forget to unwind with a glass of locally produced wine at one of Ashland’s charming wineries. Cheers to a wonderful May in Ashland!
June
When traveling to Ashland in the month of June, it’s important to dress for the warm and sunny weather. This charming town located in southern Oregon experiences an average high of 80 degrees during this time of year. I recommend wearing comfortable and breathable clothing, such as lightweight tops and bottoms made of cotton or linen. It’s also a good idea to bring a hat and sunglasses to protect yourself from the sun. And don’t forget to pack a light jacket or sweater for the evenings, as temperatures can drop to the low 50s. While exploring Ashland, be sure to wear comfortable walking shoes as the town is known for its hilly terrain. I also suggest bringing a reusable water bottle to stay hydrated throughout the day. As for activities, be prepared for anything from hiking to strolling through the town’s charming streets. I recommend packing versatile clothing that can easily transition from outdoor activities to a night out at the theater. And don’t forget to bring your camera to capture the beautiful scenery and architecture of Ashland. With the right clothing and gear, you’ll be ready to fully immerse yourself in the natural beauty and cultural experiences this town has to offer.
As summer approaches, Ashland comes alive with vibrant energy and endless activities. June is the perfect time to visit this charming town, nestled in the beautiful Rogue Valley of Oregon. The weather is warm and sunny, the flowers are in full bloom, and the locals are buzzing with excitement for the upcoming Shakespeare Festival. A visit to Ashland in June promises a delightful experience filled with culture, nature, and delicious food. One of the must-do activities in Ashland during June is attending the renowned Oregon Shakespeare Festival. This world-renowned theater festival brings together talented actors and directors from all over the country to perform classic and contemporary plays by Shakespeare and other playwrights. The outdoor Elizabethan theatre is a magical setting for a summer evening, and the performances are top-notch. Don’t forget to also explore the charming downtown area, where you can find unique shops, art galleries, and delicious restaurants. In June, the town also hosts the annual Lithia Artisans Market, where you can admire and purchase one-of-a-kind handcrafted items from local artists. With so much to see and do, a visit to Ashland in June is an unforgettable experience.
July
When visiting the charming town of Ashland in July, it’s important to dress comfortably and appropriately for the warm weather. As the temperatures can reach up to the high 80s, it’s best to wear lightweight and breathable fabrics such as cotton or linen. A hat and sunglasses are also essential to protect yourself from the sun’s rays while exploring the town. Additionally, be sure to bring a refillable water bottle to stay hydrated as you wander through the picturesque streets. While Ashland is known for its laid-back and casual atmosphere, it’s always a good idea to dress slightly more formal when attending any of the town’s renowned Shakespearean plays. Pack a nice pair of slacks or a sundress to wear to the theater, and don’t forget a light jacket or sweater for the cooler evening temperatures. As for footwear, comfortable walking shoes are a must for exploring the town’s many parks and trails. And of course, don’t forget to bring a camera to capture all the picturesque moments that Ashland has to offer.
Ashland, Oregon is a charming town nestled in the heart of the stunning Rogue Valley. While it may be known for its famous Shakespeare Festival, there is so much more to discover in this idyllic destination, especially during the summer months. In July, visitors can enjoy the warm weather and abundance of outdoor activities. Start your day by exploring the charming downtown area, filled with local shops, galleries, and restaurants. Then, take a stroll through Lithia Park, a picturesque oasis in the middle of the city, complete with lush greenery and tranquil ponds. One of the highlights of visiting Ashland in July is the annual Oregon Shakespeare Festival. This renowned event brings together talented actors from all over the country to perform classic and contemporary plays in the iconic Elizabethan Theatre. But the festivities don’t stop there – the town also hosts a variety of outdoor concerts, art shows, and farmers markets during the summer months. And for nature lovers, nearby hiking trails and the stunning Crater Lake National Park offer endless opportunities to soak in the beauty of Southern Oregon. Whether you’re a theater buff, foodie, or nature enthusiast, Ashland has something for everyone to enjoy in the month of July.
August
When visiting Ashland in the month of August, it’s important to dress for both comfort and functionality. As a popular destination for outdoor activities, such as hiking and rafting, it’s best to pack lightweight, breathable clothing. A good pair of hiking shoes or sandals is a must for exploring the beautiful trails and parks in the area. Don’t forget to bring a hat, sunglasses, and sunscreen to protect yourself from the hot summer sun. In addition to outdoor gear, it’s also important to pack clothing for the evening events in Ashland. As the home of the famous Oregon Shakespeare Festival, you’ll want to attend a play or two during your visit. Dressing in layers is key, as the evenings can get chilly. A light jacket or sweater will come in handy for those cooler nights. And for those attending the festival, a nice outfit for the theater is always appreciated. With these tips in mind, you’ll be prepared for all the adventures and cultural experiences that await you in Ashland in August.
August is a fantastic time to visit the charming town of Ashland, nestled in the picturesque mountains of Southern Oregon. The town is buzzing with energy and excitement as it hosts its annual Shakespeare Festival, one of the largest and oldest in the country. Stroll through the quaint downtown area, lined with boutique shops and delicious restaurants, and you’ll feel like you’ve been transported to a European village. And of course, no visit to Ashland is complete without catching a performance at one of the three outdoor theaters, where the talented actors bring Shakespeare’s timeless works to life under the warm summer sky. But the fun doesn’t stop there! August is also the perfect month to explore the great outdoors in Ashland. Take a hike through the lush Lithia Park, which boasts 93 acres of stunning scenery and tranquil trails. Or, for a more adrenaline-pumping adventure, head to the nearby Rogue River for some white water rafting. And after a day of outdoor exploration, be sure to unwind with a glass of local wine from one of the many award-winning wineries in the area. With so much to do and see, August is the perfect time to experience all that Ashland has to offer.
September
When visiting the charming town of Ashland in September, it’s important to dress in layers to accommodate the fluctuating temperatures. The mornings can be cool, but by midday, the sun is shining and the air is warm. I recommend bringing a light jacket or sweater that can easily be tied around your waist or placed in a backpack. Comfortable walking shoes are a must as well, as the town is filled with cobblestone streets and hilly terrain. As for what to wear, I suggest choosing lightweight, breathable fabrics such as cotton and linen. The town has a relaxed and casual atmosphere, so there’s no need for fancy attire. However, if you plan on attending a performance at the famous Oregon Shakespeare Festival, you may want to bring a nicer outfit. Don’t forget to pack a hat and sunglasses to protect yourself from the sun while strolling through the beautiful Lithia Park. And lastly, make sure to bring a refillable water bottle to stay hydrated while exploring all that Ashland has to offer.
September is the perfect time to visit the charming town of Ashland, nestled in the rolling hills of southern Oregon. As summer comes to a close, the crowds of tourists have thinned out, making it the ideal time to explore this hidden gem. One must-see attraction during this time is the renowned Oregon Shakespeare Festival, which runs from February to October. The festival showcases a variety of plays and performances, ranging from classic Shakespearean dramas to modern productions. Don’t forget to grab a picnic basket and blanket to enjoy a show under the stars in Ashland’s beautiful Lithia Park. Aside from the Shakespeare Festival, September is also the prime season for outdoor activities in Ashland. Take a hike through the stunning Cascade-Siskiyou National Monument, where you can witness the changing colors of the fall foliage. For a more leisurely activity, rent a bike and pedal along the Bear Creek Greenway, a scenic 18-mile trail that runs through the heart of the town. And for the foodies out there, don’t miss the Ashland Culinary Festival, where you can indulge in delicious local cuisine and wine while taking in the stunning views of the surrounding mountains. With its perfect blend of culture, nature, and delicious food, Ashland in September is a traveler’s paradise.
October
When traveling to Ashland in October, it is important to dress in layers. The weather can be quite unpredictable during this time, with chilly mornings and evenings and warmer afternoons. I recommend bringing a light jacket or sweater that can easily be removed as the day warms up. Additionally, comfortable walking shoes are a must as the town is full of historic cobblestone streets and hilly terrain. As for what to wear, I suggest opting for casual and comfortable clothing. Ashland is a laid-back town and you’ll fit right in with jeans, a t-shirt, and a light jacket. However, if you plan on attending a performance at the renowned Oregon Shakespeare Festival, it is customary to dress slightly more formal. A nice pair of slacks or a dress for women will be appropriate for the occasion. Lastly, don’t forget to bring a reusable water bottle and a small backpack to carry any essentials you may need while exploring this charming town. Happy travels!
October is a fantastic time to visit the charming town of Ashland in southern Oregon. As the leaves turn vibrant shades of red, orange, and yellow, the town comes alive with a plethora of autumnal activities and events. One of the highlights of the month is the famous Ashland Independent Film Festival, showcasing independent films from around the world. With screenings, Q&A sessions with filmmakers, and panel discussions, it’s a must-visit for any cinephile. Additionally, the town’s annual Shakespeare Festival continues into October, offering a chance to catch some of the Bard’s most beloved plays in the beautiful outdoor theater. Aside from the cultural offerings, October is also a great time to explore Ashland’s natural beauty. The nearby Lithia Park boasts stunning foliage, perfect for a leisurely stroll or a hike among the changing leaves. For a more adventurous activity, head to the nearby Mt. Ashland for some early season skiing or snowboarding. And of course, no visit to Ashland would be complete without sampling some of the local cuisine. From farm-to-table restaurants to cozy cafes, the town offers a diverse array of dining options that showcase the best of Oregon’s culinary scene. So pack your scarves and jackets and join me in experiencing the magical charm of Ashland in October.
November
November is a lovely time to visit Ashland, Oregon. The weather is crisp and cool, making it the perfect time to explore the charming streets and stunning natural surroundings. When packing for your trip, be sure to bring layers. The mornings and evenings can be chilly, but the afternoons can warm up significantly. A light jacket, scarf, and comfortable walking shoes are essential. Don’t forget to pack an umbrella or rain jacket as well, as November is known for its unpredictable showers. When dressing for a day of sightseeing in Ashland, opt for comfortable and casual attire. The city has a laid-back vibe, so leave the fancy clothes at home. Jeans, a cozy sweater, and a pair of comfortable shoes will be your go-to outfit. If you plan on attending a play at the renowned Oregon Shakespeare Festival, dress slightly nicer, but still stick to a comfortable and practical ensemble. And don’t forget to bring a reusable water bottle and a small backpack to carry any souvenirs or snacks for your adventures. Now you’re ready to experience all that Ashland has to offer in style and comfort.
Welcome to Ashland, Oregon, a charming little town nestled in the heart of the beautiful Rogue Valley. While many travelers flock to this area during the summer months for the renowned Oregon Shakespeare Festival, November offers a unique and peaceful experience for those looking to explore this hidden gem. One of the must-do activities during this time of year is to take a stroll through Lithia Park, a picturesque oasis in the center of town. The fall foliage is at its peak, creating a breathtaking backdrop for a leisurely walk or a picnic lunch. And if you’re lucky, you may even catch a glimpse of the resident deer that call this park home. November also marks the start of the holiday season in Ashland, and the town comes alive with festive events and activities. Make sure to visit the annual Festival of Light, where the entire downtown area is illuminated with thousands of twinkling lights. It’s the perfect opportunity to get into the holiday spirit and do some early Christmas shopping at the local boutiques and art galleries. And for the foodies out there, don’t miss the Ashland Culinary Festival, where you can sample delicious dishes from the region’s top chefs. So come and experience the cozy charm of Ashland in November, and you’ll see why this town is a year-round destination for travelers seeking a unique and authentic Oregon experience.
December
As the holiday season approaches, Ashland is a charming destination to experience the magic of winter. However, with temperatures dropping and potential snowfall, it’s important to come prepared. For a comfortable and practical travel experience, I recommend dressing in layers when visiting Ashland in December. Start with a base layer of thermal clothing, followed by a cozy sweater or fleece, and top it off with a waterproof jacket. Don’t forget to bring a warm scarf, gloves, and a hat to keep you warm while exploring the town. Comfortable walking shoes with good traction are also essential, as the streets can get slick from snow and ice. When it comes to what to wear, I suggest opting for warm and comfortable clothing that can be easily layered. Ashland is known for its casual and laid-back atmosphere, so leave your fancy dresses and heels at home. Instead, pack items like jeans, leggings, and comfortable sweaters that you can mix and match. And don’t forget to bring a pair of waterproof boots for those snowy days. As for accessories, bring a small crossbody bag to carry your essentials while exploring the town. And of course, don’t forget to pack a camera to capture the picturesque winter scenery in Ashland. With the right wardrobe and gear, you’ll be all set to enjoy a cozy and festive winter getaway in this charming town.
December is a magical time to visit the charming town of Ashland. The crisp air and twinkling lights create a cozy atmosphere that is perfect for exploring the town’s many holiday activities. One must-see event is the Oregon Shakespeare Festival’s production of “A Christmas Carol”. This heartwarming adaptation of the classic tale is sure to put you in the holiday spirit. After the show, take a stroll through downtown Ashland and admire the festive window displays while sipping on a hot cocoa from one of the local cafes. For a unique experience, visit the Ashland Art Center’s annual “Deck the Walls” exhibition. This showcase features the work of local artists and is the perfect place to find one-of-a-kind gifts for your loved ones. Afterwards, head over to Lithia Park and take a horse-drawn carriage ride through the snow-covered trees. The park is also home to the Festival of Light, a spectacular display of over one million lights. Whether you’re a theater lover, art enthusiast, or just looking for some holiday cheer, Ashland has something for everyone in the month of December.
Hey there! I’m Jason, a total travel junkie who is always on the go. I live for discovering new places, meeting cool people, and experiencing different cultures. I’m here to help you with your travels.
